cyclooctakis-(1->4)-2,6-di-O-allyl-α-D-glucopyranosyl | 214958-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclooctakis-(1->4)-2,6-di-O-allyl-α-D-glucopyranosyl
• 英文别名: per(2,6-di-O-allyl)-γ-cyclodextrin
• CAS: 214958-24-4
• 化学式: C₉₆H₁₄₄O₄₀
• 分子量: 1938.18
• InChiKey: VNVWSDRFJIKXGA-LABSLJFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  136.0
• 可旋转键数：
  56.0
• 环数：
  30.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  457.2
• 氢给体数：
  8.0
• 氢受体数：
  40.0

反应信息

• 作为产物：
  描述：

  3-氯丙烯 、 γ-环糊精 在 barium hydroxide octahydrate 、 barium(II) oxide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以22%的产率得到cyclooctakis-(1->4)-2,6-di-O-allyl-α-D-glucopyranosyl
  参考文献：
  名称：

  Regioselective allylation of cyclomaltoheptaose (β-cyclodextrin) leading to per(2,6-di-O-hydroxypropyl-3-O-methyl)-β-cyclodextrin

  摘要：

  The selective modification of cyclodextrins remains a real challenge to obtain well-defined structures. The targeted cycloheptakis-(1 -> 4)-2,6-di-O-hydroxypropyl-3-O-methyl-alpha-D-glucopyranosyl [per(2,6-di-O-hydroxypropyl-3-O-methyl)-beta-CD] was obtained by a three-step procedure. The selective allylation of the hydroxyl functions at the positions 2 and 6 was used as a first step. This reaction was revisited then enlarged to a and gamma-CDs to determine new conditions for a one-step synthesis in high yield. The per(2,6-di-O-allyl)-beta-CD derivative was then reacted with iodomethane to provide per(2,6-di-O-allyl-3-O-methyl)-beta-CD. Oxidative hydroboration of the allyl functions was then carried out in order to obtain a new CD derivative with seven primary hydroxyl functions on each side of the truncated cone, having a similar reactivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.033